4,7-二溴[1,2,5]噻二唑并[3,4-d]嘧啶的安全合成及其 SAr 反应。
Safe Synthesis of 4,7-Dibromo[1,2,5]thiadiazolo[3,4-]pyridazine and Its SAr Reactions.
机构信息
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian.
Nanotechnology Education and Research Center, South Ural State University, 454080 Chelyabinsk, Russia.
出版信息
Molecules. 2018 Oct 9;23(10):2576. doi: 10.3390/molecules23102576.
A safe and efficient synthesis of 4,7-dibromo[1,2,5]thiadiazolo[3,4-]pyridazine from the commercial diaminomaleonitrile is reported. Conditions for selective aromatic nucleophilic substitution of one or two bromine atoms by oxygen and nitrogen nucleophiles are found, whereas thiols formed the bis-derivatives only. Buchwald-Hartwig or Ullmann techniques are successful for incorporation of a weak nitrogen base, such as carbazole, into the [1,2,5]thiadiazolo[3,4-]pyridazine core. The formation of rather stable S…η²-(N=N) bound chains in 4,7-bis(alkylthio)-[1,2,5]thiadiazolo[3,4-]pyridines makes these compounds promising for the design of liquid crystals.
从商业二氨基马来腈出发，安全有效地合成了 4,7-二溴[1,2,5]噻二唑并[3,4-d]哒嗪。找到了通过氧和氮亲核试剂选择性取代一个或两个溴原子的条件，而硫醇仅形成双衍生物。Buchwald-Hartwig 或 Ullmann 技术可成功地将弱氮碱（如咔唑）引入[1,2,5]噻二唑并[3,4-d]哒嗪核心。在 4,7-双（烷基硫基）-[1,2,5]噻二唑并[3,4-d]哒嗪中形成相当稳定的 S…η²-（N=N）键链，使这些化合物有望用于设计液晶。
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